Phthalimide → 3-(3-(1,3-Dioxoisoindolin-2-yl)propyl)benzaldehyde

HRID 242707Notes

Reaction equation

HRID 242707 reaction equation
[C:1]1(=[O:11])[NH:5][C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[OH2:12].[C:13]1([CH3:23])[CH:18]=[CH:17][C:16](S(O)(=O)=O)=[CH:15][CH:14]=1.[CH3:24][C:25]([CH3:27])=O.O>>[O:6]=[C:4]1[C:3]2[C:2](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:1](=[O:11])[N:5]1[CH2:16][CH2:17][CH2:18][C:13]1[CH:23]=[C:25]([CH:27]=[CH:15][CH:14]=1)[CH:24]=[O:12]

Participants

4

Reactant 3

HCID 6809PhthalimideHCID 521998p-Toluenesulfonic acid monohydrateHCID 18366337Propan-2-one--water (1/1)

Product 1

HCID 577664653-(3-(1,3-Dioxoisoindolin-2-yl)propyl)benzaldehyde

Procedure

To a solution of phthalimide 50 (5.66 g, 16.67 mmol) in acetone-water (5:1, 50 mL) was added p-toluenesulfonic acid hydrate (0.2116 g, 1.11 mmol). The mixture was stirred for 3 h then concentrated under reduced pressure. The residue was partitioned between EtOAc and water and the combined organics were washed with brine, dried over MgSO4 and concentrated under reduced pressure to give phthalimide 29 as a white solid. Yield (4.48 g, 92%). The NMR data was consistent with data reported above.

Workup

  1. concentrationthen concentrated under reduced pressure
  2. customThe residue was partitioned between EtOAc and water
  3. washthe combined organics were washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-73db8925cdd745cb8738b9bd8b6da10e
Source dataset
uspto-grants-2014_02
Patent number
US08653142B2

Reaction notes

Loading…